


Friends, Family, and Sex Kitten Exes

by CrashDevil (cjdevlin19)



Series: A Hard Ten Series [2]
Category: Supernatural
Genre: Christmas Party, Drug Addiction, F/M, Male Escort, Self Esteem Issues
Language: English
Status: Completed
Published: 2018-12-03
Updated: 2018-12-03
Packaged: 2019-09-06 11:24:22
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,766
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16831657
Author URL: https://archiveofourown.org/users/cjdevlin19/pseuds/CrashDevil
Summary: Sam introduces y/n to his friends and Dean, then takes her to the escort service’s Christmas party, where she meets the rest of the Winchesters… and Sam’s ex-girlfriend.~~~~~~~~~~~~“You’re gonna love Jo and Billie, and Meg, oh and at least one of the Rubies. Are you gonna let me see any of these dresses you’re trying on?”“They look bad, Sam. I look bad,” you groaned.“Shut up. Let me in,” Sam demanded, his voice low and resolute.You rolled your eyes and twisted the handle to pop the lock. He slipped into the dressing room, taking up far too much space in the little cubicle, and you gestured at the red dress with the lace neckline. “See?”“What’s wrong with it? It looks amazing on you.”“Yeah, it’d be fuckin’ perfect if it weren’t still half-unzipped in the back and did you say ‘Meg and the Rubies’?” You finished, eyes going wide.Sam motioned for you to turn so you spun around. “Yeah, the ladies from our sister site, ‘Ellen’s Southern Sex Kittens’ are gonna be at the party. It’d be a sausage fest without ‘em.” He ran his hand down the bare skin of your back until his fingers reached the zipper.





	Friends, Family, and Sex Kitten Exes

**Author's Note:**

  * Inspired by [A Hard Ten and a Soft Four](https://archiveofourown.org/works/16632365) by [CrashDevil (cjdevlin19)](https://archiveofourown.org/users/cjdevlin19/pseuds/CrashDevil). 



Friends, Family, and Sex Kitten Exes

  


**Author’s Note:** This is a sequel to **[A Hard Ten and a Soft Four](http://crashdevlin.tumblr.com/post/180146681258/a-hard-ten-and-a-soft-four), **part two of my ‘Whore for the Holidays’ series (and I’m sorry about that name, lol). Also, I’m sorry if you like Adam, because I made him a dick in this.

 **Summary** : Sam introduces y/n to his friends and Dean, then takes her to the escort service’s Christmas party, where she meets the rest of the Winchesters… and Sam’s ex-girlfriend.

 **Pairing(s)** : Sam x plus size!Reader, mentions of Sam x Ruby (past), Dean x Reader (barely)

 **Story Warnings** : **18+** **HERE BE SEX, DO NOT READ IF YOU’RE A YOUNG’UN!,** prostitution, semi-public fingering, oral (male and fem rec), protected sex, cheating (if you count a kiss as cheating), mentions of drug addiction, self-esteem issues

  


* * *

“I can’t believe you’re dating a client, man. That is, like, Rule #2 in this business,” Ash chided.

“Right behind ‘Wear a Condom’ and right before ‘Don’t Tell Them Your Real Name’,” Arthur, or Ketch as he was known to his associates, supported.

“Look, I don’t expect you guys to understand this, but y/n is amazing.”

“If she were amazing, why did she need Bobby’s help in the first place?” Fergus asked, flopping down on Sam’s couch.

“Because she’s an introvert and dating is hard and her family, with some rare exceptions, are some of the most overbearing and stifling people I’ve ever met.” Sam sighed, loudly, looking around his living room to see what else he could clean before his other guests showed up.

“Lay off, guys. If she’s good enough for my little brother, she’s good enough for all of us.” Dean walked in, handing out beers. “But know that we’re going to be merciless if she’s an idiot, or something.”

“She’s not an idiot, Dean. She’s an architect. She’s great, but I’m nervous about you guys scaring her away so tone down the bullshit, okay?”

“How would we possibly scare her away?” Fergus asked, a fake tone of offense on his words.

“Almost _anything_ from you, dude.” Dean teased.

“Just… everybody be nice, okay?” Sam almost begged.

“We’ll be good.” Ketch threw up three fingers in a mock ‘Scout’s Honor’ and twisted open his beer as Sam’s doorbell rang.

Sam took a deep breath, looked around the living room again and walked to the door. He smiled when he opened the door to see you and your redheaded best friend. “Hey.”

You smiled back. “Hey. This is Charlie.”

Sam nodded. “I hear we have you to thank for our meeting each other,” he said, offering his hand, which she took.

“Damn straight. I will take your thanks in the form of Funko Pop figures and tickets to the next new Star Wars movie in IMAX,” she said, pushing her way into the apartment.

You chuckled. “I’ve got the movie covered, but she still needs a Supreme Leader Snoke figure, so you can track that down for her.” You looked around his massive frame to try to see his living room. “How many showed up?”

“Three, and my brother. That’s okay?”

“Yeah.” You nodded and stepped into apartment.

“Guys, this is y/n and her best friend, Charlie. This is Fergus, Ash, Ketch, and my brother, Dean.”

“It’s nice to meet you.” You smiled at them, especially Dean who stood and offered his hand, covering yours in both of his.

“You, too, sweetheart. Sam hasn’t been able to keep his mouth shut about you for the last few weeks.”

Sam gave a tight smile. “Thanks, Dean.”

“No problem, little brother.” Dean smirked as he let your hand go and dropped down into a recliner. “So, what’re we watchin’?”

“Well, I _was_ gonna put on _Deathly Hallows: Part Two_ but y/n reminded me that not everyone is as big a geek as we are, so I figured we’d go with an indisputable classic sci-fi action movie. _Terminator 2: Judgment Day_.”

“I dunno. I always get distracted by the shitty time travel logic.” Ash argued.

“You wanna talk about shitty time travel logic, let’s put on _Heroes_ , which changes its approach to time travel, vis-a-vis consequences of stepping on the damn butterfly, between seasons and sometimes _during_ seasons.” You smiled as Sam handed you and Charlie each a beer and picked up his remote as you sat down between him and Charlie.

“Yeah, but _Heroes_ gave us Zachary Quinto, though. Gay icon.” Charlie said.

“Well, he’s gay and he’s awesome, but I don’t know if he’s an _icon_.” Ketch argued.

“Freddie Mercury. _That_ was a gay icon.” Fergus provided.

“That’s categorically _false_.” You snapped. “Freddie was a noted bisexual. Gay men have been erasing him for decades, but he was bi as evidenced by the girlfriend he had for half his life. Just because gay men needed a famous face, they stole him, but even Brian May says Freddie wasn’t _gay_.”

“Maybe Mary Austin was just-” Fergus started, but Charlie put her hand up to stop him.

“Don’t call Mary Austin a ‘beard’. Y/n is super woke about erasure and the whole thing is a huge deal for her.”

“ _Anyway_.” Sam said, loudly. “ _T2_.”

“Yeah. Let’s go.” Dean kicked his feet up on Sam’s coffee table as Sam pulled you closer into his side and started the movie.

“Ooh, badass Linda Hamilton.” Charlie cooed when it got to mental asylum scenes.

“Ugh, this fuckin’ shrink, though. Him being crazy in the third one is the _only_ redeeming quality of the third one.” You commented.

“Are you hens gonna peck through the entire movie?” Ketch asked, irritated.

You gasped, dramatically. “I’m so sorry, Arthur.” You gave a mocking look of pity. “Sam didn’t tell me that you were that special kinda slow where you have to pay undivided focus to a movie you’ve seen a hundred times in order to understand it. Of course, we’ll be quiet so that you can understand the movie.” You rolled your eyes and did a jerk-off motion with your hand. “Wanker.”

Dean snorted, loudly. “If you don’t marry this woman, Sammy, I will. She’s fucking great.”

Sam smiled proudly down at you. “Sorry, Dean. She picked me.”

“She almost picked Dean, though.” Charlie said, taking a drink of her beer.

Dean’s eyebrows shot up. “Oh, really?”

“Charlie!” You admonished.

“What, you didn’t think I noticed you bookmarked Dean’s page? Bitch, you were on my laptop!”

“You think my brother’s hot, y/n?” Sam asked, with a playful smirk on his lips.

You returned the smirk. “What kind of question is that, Sam? Of _course_ I do. _Look_ at him.” You giggled. “But I chose _you_ , baby. The world’s best lawyer-whore.”

“Think he’s the world’s _only_ lawyer-whore,” Dean quipped.

You snuggled closer to Sam and he wrapped his arm around you. “I’m really glad I picked you,” you whispered, making him smile.

“Me, too.” He smirked as he brought his Coke bottle to his lips.

When the movie was over Ash, Fergus and Ketch left and Sam walked you to your car. “So, they weren’t so bad, were they?”

You shook your head. “Just like the douchebags _I_ work with.”

“So, you’re gonna come with me to the Christmas party, right?” he asked, pushing you into your car door and leaning over you. “Love to see you get all dressed up. Show you off to all the guys from work.”

“Suppose I owe you, huh?” You reached up and ran your hands through his hair, tucking your hands behind his head. “Since you came and met my family, had to deal with Marlene and Carol and the guys staring at your crotch all weekend.”

“We got ‘em back by disturbing their sleep every night, though.” He whispered, leaning his head down and running the tip of his nose down the length of yours. “You got a dress to wear?” He expertly brought the conversation back to the point he wanted it to be.

“Um…”

“We’ll go shopping.”

“Yeah, you guys are super cute and all, but I’m freezing my frakin’ ass off over here. Can you, at least, unlock the damn car?” Charlie called out across the car.

Sam pulled away so you could pull your keys out of your pocket and hit the button to unlock the car. “Get your ass in the fraking car,” you called over your shoulder.

Sam chuckled. “I always liked ‘frell’ better as a substitute for ‘fuck’.”

You gasped. “Oh, be still, my heart. You know _Farscape_? Can you get any more perfect?”

He laughed, loudly. “I could _try_.” He leaned down and pressed his lips to yours, making you moan and wrap the hand that wasn’t holding the keys in the fabric of his coat.

“Fuck, Sam. Your kisses are frelling magic.” You looked up into his eyes. “I’ll try to get a dress tomorrow.”

“No, I wanna go with you.” He pulled away, running his hands down your arms to grab your hands. “But I… I have a client tomorrow. Her husband’s out of town so she’s bought the whole day. I’m free the day after.”

“Unless a client calls.” You said it without letting bitterness cloud your words.

“No. I won’t take any clients Sunday, okay? I promise.” You nodded, leaning up to press your lips to his. “And we can go out to dinner somewhere after we find you a perfect dress, huh?”

“Yeah. I’ll see you Sunday, babe.” You squeezed his hands and spun away to open your car door and slide in.

“You two are so cute it’s disgusting.” Charlie muttered, making you chuckle.

“You’re just jealous. Get a girlfriend, then you won’t be so hateful.” Charlie just rolled her eyes as you waved at Sam and reversed out of the parking space, heading home.

Sam walked back into the apartment and started to grab plates and bowls from the snack food. “So, that’s y/n, huh? She’s awesome.” Dean said, helping Sam clean up from the get-together.

Sam nodded. “Yeah, she is.”

“I mean, if that woman was an introvert, you’re already working wonders on her.”

“Not happening, Dean.” Sam didn’t even look at his brother as he set dishes in the sink.

“What?” Dean asked, innocently.

“You’re going to suggest a three way. It’s not gonna happen, dude.”

“Wha- a three- I don’t- yeah, I was.” Dean finished, smirking. “Come on, man. She’d be into it.”

”Well, _I’m_ not into it.”

“We’ve done it _before_.”

Sam sighed, finally turning his hazel eyes on his older brother. “She isn’t one of the women off of my client list. She’s special. She’s the first _real_ girlfriend I’ve had since Jess left me. Please, just let me have something good that’s mine.”

Dean scoffed. “I wasn’t tryin’ to _take_ her, just, you know…” He shook his head. His gaze went soft. “You’re really into this chick, aren’t you?”

“Yeah, Dean, I am. So… just back off, okay?”

Dean nodded. “Yeah, okay. Backing right the hell off.”

Sam smiled, gratefully. “Thanks.”

“Yeah, well, if she’s got a friend that’s not a lesbian, it’d be cool of you to introduce me.”

“You got it, Dean. Hey, take the beer when you leave.”

~~~~~~~~~~~~~~~~~~~

“I can’t wait to show you off.” Sam’s voice from the other side of the dressing room door in Torrid didn’t do anything to make you feel better about the fact that this was the third dress you tried on, all _supposedly_ in your size, which did not fit. “You’re gonna love Jo and Billie, and Meg, oh and at least one of the Rubies. Are you gonna let me see any of these dresses you’re trying on?”

“They look _bad_ , Sam. _I_ look bad,” you groaned.

“Shut up. Let me in,” Sam demanded, his voice low and resolute.

You rolled your eyes and twisted the handle to pop the lock. He slipped into the dressing room, taking up far too much space in the little cubicle, and you gestured at the red dress with the lace neckline. “See?”

“What’s wrong with it? It looks amazing on you.”

“Yeah, it’d be fuckin’ perfect if it weren’t still half-unzipped in the back and did you say ‘Meg and the Rubies’?” You finished, eyes going wide.

Sam motioned for you to turn so you spun around. “Yeah, the ladies from our sister site, _**‘Ellen’s Southern Sex Kittens**_ ’ are gonna be at the party. It’d be a sausage fest without ‘em.” He ran his hand down the bare skin of your back until his fingers reached the zipper.

“They’re not shy about that name, are they?” You were a little breathless just from that small caress.

“No, they are not.” He chuckled, adjust the dress before starting to pull the zipper up. “They’re really nice, though. Most of ‘em. Meg’s a bit of a bitch, but with a few drinks and Cas’ calming influence, she’s got a real soft side.” The dress tightened as he zipped it but he got the thing zipped and stepped away. “How’s that?”

You smoothed your hands down the front of it and turned to the mirror. “It doesn’t look bad.”

“It looks fuckin’ _great_ , but how does it make you _feel_ , baby?”

Your eyes caught his in the mirror, looking at you with all that adoration and lust. “Well, when you look at me like that, I feel like a supermodel, so any dress that makes you do that makes me feel amazing.”

He stepped back further, giving you space. “Okay, twirl. Let’s see how that skirt moves.” You giggled and spun in a quick circle. He smirked. “Perfect. Now, just one more test.” He stepped close again, wrapped his left arm around you and quickly slipped his right hand under your skirt, rubbing his fingertips along your panty-covered slit.

“Sam!” you squeaked.

“Shh! This is a sex offense if we get caught and I don’t want your pretty face on that fuckin’ registry.”

“Then, stop,” you whispered, fearfully. Ending up on the Sex Offender Registry because you couldn’t resist your super-hot boyfriend was not in the least bit okay. It would ruin you. “Sam.”

“I just wanna taste you. Just real quick, before you take the dress off.” He rubbed your clit and you had to swallow down a whimper. “Can I taste you, y/n?”

“I’m scared.”

“That’s half the fun, and if we get caught, you’ve got a good lawyer.” He hadn’t stopped his fingers’ work, and the need for release was quickly overtaking your fear.

“Oh, god, please don’t let us get caught.” You whispered and Sam took that as consent, dropping to his knees and disappearing under the skirt of the dress. You grabbed the closest coat hook with your left hand and covered your mouth with your right hand, trying to keep your sounds inside of you as he pulled your underwear to the side and attached his mouth to you, tongue slipping between your pussy lips and swirling around your clit. You squeezed your eyes closed, hard, as he slipped a finger in your entrance.

It didn’t take long for you to cum, just a few good pumps and a crook of his finger into that patch of spongy flesh inside of you while lapping at your clit, and when he stood licking his lips, he was smirking at you. “Get that dress. That’s a _great_ dress,” he said, reaching around to unzip it before slipping out of the dressing room, leaving you breathless and tingling all over.

~~~~~~~~~~~~~

You always felt safe in Sam’s arms, secure in yourself and your place with him. He made you feel like the only woman in the world… that is, until his phone inevitably rang.

Sam smiled, apologetically as he pulled away from you to grab his phone. He walked into his bedroom’s ensuite bathroom as he answered. “Delia. What can I do to you tonight, baby?” You swallowed down the jealousy at his flirty tone and took a deep breath as you looked in the mirror. It was just an act with them. Not with you. You were the one in his heart, he was the one in their beds. What kinda name is _Delia_ , though?

Okay, so you were jealous of Delia… and Michelle and Olga and Francesca. You knew what you were getting into and you tried to ignore the fact that he fucked so many other women, but it was really fucking hard to ignore when they kept cutting into _your_ time with him. You rolled your eyes and kicked your feet over the edge of his bed, searching for your leggings. You found them in the corner of his room, draped over his lamp. You were pulling your beige tunic shirt on and searching for your shoes by the time he made it out of the bathroom.

“Going somewhere?” he asked, leaning against the wall in all his naked glory that you purposely didn’t look at because if you did, you’d just want to get back in bed and then you’d have to deal with him leaving for his date with _Delia_ and you couldn’t. You just couldn’t.

“Yeah. I’m gonna go take that dress home, start looking for some shoes to pair with it and I’ve got an early day tomorrow. I have to present some plans to the mayor and watch him pretend like he knows how to read blueprints when I should just be showing them to the city planner, but he’s not powerful enough to approve what I need, so-”

“You’re rambling. Are you okay, y/n?” Sam stepped closer, but you dropped to your hands and knees to pull your shoes out from under his bed.

“Yeah, Sam. I’m just… kinda touched-out and overwhelmed with today. I need some time. I’ll see you… party’s on the twentieth, right?”

“Whoa, you need a _week and a half_ of time?” Sam’s eyes were wide when you looked up at him.

“No?” You slid your feet into your shoes and stood, trying the word again without the upward inflection. “No, not a week and a half. I was just confirming that’s the date. I’ll text you.” You went to your tiptoes, pressed your lips to his cheek and rushed past him, leaving him standing in the middle of bedroom with confusion on his face.

~~~~~~~~~~~~~~~~~~~~~~~~~

“I don’t know. Maybe she _can’t_ handle the job. I mean, I thought we were doing good, but…” Sam ran his hand down his face, then looked up and took the ginger ale his father offered. “I mean, I thought we could get this to work. You and Kate do it.”

“Kate and I are different, Sam. Kate wasn’t a client and she was very firm on her limits when she found out what I did. Maybe y/n should have a conversation with your stepmom. Or maybe _you_ should. You need to find ways to make y/n more comfortable.”

“Turn the damn phone off,” Kate said, walking in and sitting next to John with a beer in her hands. “Her time with you needs to be _her_ time, no one else’s. She knows what you do, Sam, but that doesn’t mean she wants it shoved in her face every time she’s with you. So, just give her your whole and undivided when you’re with her, that’s gonna be the biggest part of keeping her.”

Sam sighed, closing his eyes in realization. “Delia called when she was over. Of course.”

“You’re gonna wanna fix that.” John said with a nod.

“Yeah. Uh. Thanks for the advice… and the drink.” Sam set the bottle on the coffee table and stood, leaning down to hug Kate before nodding at John and rushing out to his pickup truck. Sam drove to your office and watched you through the window from the parking lot for a few minutes. You were arguing with someone in a black suit, gesturing with a stack of papers.

That dark protective instinct flared up when the man slapped the papers out of your hand and got in your face, yelling loudly enough that he was spitting in your face. Sam jumped out of the cab of his truck, intent to rush in and help you, but stopped when he saw you just wipe the spit off of your face and slap your damp hand across the man’s face. You yelled something at the man when his eyes went wide and his hand went over his cheek. He scrambled out of the building, trying to look like he hadn’t just been taken down a peg by a woman. Sam watched him fling himself into a Jaguar and drive off before he ventured into your office.

You were down on your knees, cleaning up the papers, when Sam walked in. “Hey.”

Your eyes snapped up to his. “Hey. Wh-what are _you_ doing here?” You straightened, setting your papers on your drafting table and turning to him.

“I was coming to see you, to apologize about yesterday. I realized what made everything go to shit last night. Wasn’t expecting to see you in a fight. What was that about?”

You turned a bit red as you looked away from him, rubbing the back of your neck. “Uh, that’s David Crist. He’s a partner at my competitor. Basically, that was just a very uncivil business conversation about why I’m not giving them my fuckin’ contract with the city to design the new DMV.”

“Well, you handled yourself… _amazingly_.” Sam praised, a look of bafflement on his face.

You shrugged. “I know my business and I’m not going to be intimidated into dropping a contract just because some dude comes in and gets in my face. Besides, Thornton-Crist Concepts would butcher the building. Their egos know no bounds. They’d waste a bunch of money on frills and bullshit and- why are you smiling like that?”

“You’re so amazing.” He reached out, cupping your cheek in his left hand.

You looked up into his eyes, lost in the kaleidoscope of colors. “Wh-why were you here, again?”

“To kiss you silly and apologize for taking calls when I said Sunday was just for you.” He said, leaning down to bump the tip of his nose against yours.

“Oh,” you breathed out.

“I’m so sorry, babe. Forgive me?”

“I don’t seem like a crazy jealous stupid-because-I-already-knew-about-all-the-other-women-”

He cut you off with his lips against yours, his hand sliding into your hair to pull you harder against his mouth. When he pulled back, he was smiling again. “Not crazy, and rightfully jealous. Your time should be yours, okay, and I get that, babe. I’m sorry. I’m gonna tell Bobby, from now on, the work phone is off when I’m with you.”

You almost sobbed. You held it in by taking a deep breath and pressing your lips to his. “You’re a-fuckin’-mazing, you know that?”

“I take it that means you accept the apology?” He chuckled.

“Yes, you dork, I accept.” You sniffled, pulling back from him. “I do have to get back to work, though.”

Sam smiled, hugged you tightly, and stepped back. “Okay. Get back to work. I’ll call you tonight.” You nodded, waving at him before looking down at the papers stacked on your drafting board.

~~~~~~~~~~~~

When you answered your apartment door on the twentieth, wearing the dress and a pair of black platform heels with your hair professionally done in a elegant updo and makeup that took an hour and a half and four separate YouTube tutorials to get right, Sam’s jaw hung open. “Holy shit.”

You smiled and looked down. “It’s okay, then?”

“Better than okay.” Sam answered.

“I told her she looked hot as fuck, but I guess the lesbian’s opinion doesn’t matter.”

“Hi, Charlie.” Sam called over your shoulder to the redhead, who waved from the couch without looking up from her laptop screen. His eyes dragged down your figure again, not knowing where to focus. “She’s right, you look hot as fuck.”

“Well… good. That means the _hours_ I spent on this look were worth it.” Sam smiled and offered you his arm. “Oh, yeah, definitely gonna need help to the car. These heels are about two inches higher than any heel I’ve worn before.”

“It’s kinda weird… you’re only, like, a foot shorter than me, now.” He joked.

You laughed, slapping your hand against his chest. “Jerk.”

“No, that’s Dean, not me.”

The party was at a large house, though not quite so large as Maw-maw’s manor, and there were already many people milling around with drinks in their hands. The women were all gorgeous and you tried not to notice that you were literally the only one who could be described as plus-size. Sam certainly didn’t seem to notice. Dean was across the living room, talking to John, Kate, Adam and two women, one in a skimpy dress and the other in jeans and a red blouse. Dean’s eyes lit up when he saw you and Sam.

“Sammy! y/n! Lemme grab you drinks. Eggnog?” He didn’t wait for an answer before he rushed to the wetbar.

Sam smiled at everyone as you came to a stop in front of the group. “Guys, this is my girlfriend, y/n. Y/n, this is my dad John, my stepmom Kate, little brother Adam.” He gestured from each person, then to the two women. “And this is Ellen, Bobby’s wife, and her daughter Jo.”

“It’s nice to meet you all,” you said, smiling as Dean walked up and handed you a cup of eggnog and Sam a bottle of water. You grimaced at the taste. “That is strong!”

“Yeah… Bobby’s a little heavy-handed on the booze. Sorry, I forgot to warn ya,” Dean apologized.

Adam’s eyes were on you, hadn’t left since you walked up, and they were making you uncomfortable. “I don’t get it,” he finally said as John was telling you that he used to be a Marine. Everyone turned their attention to the youngest Winchester and your stomach tied in a knot. He was looking at you like your family always did. Something destructive was about to come out of the teen’s mouth.

“Adam, don’t.” Kate scolded, quietly.

“No. They were both raving about this chick and she’s a cow.” He was defiant, staring you down, and Sam moved to step in front of you, but you grabbed his arm.

“Don’t.” Your voice was soft. You took a deep breath. “He’s your brother and he’s just a stupid kid. No more mature than TJ, obviously.” You downed the rest of the strong eggnog and shivered. “Where’s the bathroom?”

Sam directed you to the restroom and watched as you disappeared down the hall before turning to Adam. “What the fuck’s wrong with you?” he growled.

“ _What_? You’re the one dating a fat-ass. What’s wrong with _you_?” Adam spat back.

“You need to shut your face, kid, or you’re gonna get your ass handed to you by your _much_ bigger brothers.” Dean threatened.

“Adam, walk away, son.” John instructed, grabbing the youngest man’s arm and walking away with him. “Let’s talk.”

Sam sighed, angrily. “I swear, I don’t know how that kid’s a fuckin’ Winchester.” He shook his head. “Sorry, Kate. I mean-”

“No, it was completely uncalled for. She seems lovely, Sam.”

“She _is_. She’s great. She didn’t deserve that shit. What crawled up _his_ ass?” Dean asked, looking around the party for some sign that you were coming back.

Kate shrugged, shaking her head. “I don’t know, boys. But your father will find out, you know he will.”

“The party has arrived!” A voice at the entrance made everyone turn. The blond and brunette duo of Ruby and Ruby Two were walking in, turning heads as always, as you reentered the living room and walked up to the Winchesters.

“Well, _they_ know how to command attention,” you commented, eyes on the women.

“Yeah. The Rubies are very good at that, ain’t they, Sam?” Ellen responded.

“Uh.” The way his face seemed to tinge pink made you blink and turn back to look at the women. They were gorgeous, thin, curved only in the places a man wants curves… for lack a another term, they were better. “Yeah. That’s their job.”

“I’m gonna go get some more eggnog.” You said, quietly, before walking away again.

Dean followed you with his eyes, noticing your eyes were glued to the Rubies. He turned to Sam. “Dude, tell me she knows that you and Ruby Two were an item.”

“What? No, dude, Ruby and I weren’t an item. It was just sex.”

Dean’s eyes went wide. “This is the woman who got you hooked on-”

“Dean.” Sam’s eyes narrowed and Dean shook his head.

“That wasn’t just sex, Sam. You may not have _dated_ Ruby, but you had a _relationship_.” Dean stepped closer to his brother. “And you knew she was gonna be here and you didn’t give y/n forewarning?” He gestured at the bar as inconspicuously as possible. “That woman is already feeling inadequate and you didn’t tell her that a bitch you used to fuck, not for money but for fun, was gonna be here? Come on, man, you’re supposed to be the _smart_ one.”

“Winchesters!” Ruby Two squealed as she walked up, Ruby following.

“Ruby.” Dean nodded at the blond before glaring at the brunette. “Bitch.”

“Dean, clever as always.” Ruby Two teased before turning to Sam. “Hi, Sam.”

“Ruby.” Sam greeted, tightly. Ruby put her hand on his chest and licked her lips. He grabbed her wrist and pulled her hand away from him. “No one said you could touch me.”

She laughed, amused, and slightly confused. “It’s never been a problem before.”

“I have a NA sponsor, now… and a girlfriend.” Sam dropped her hand.

“A girlfriend? Really?” Ruby Two looked around. “Where is she? I’d love to meet her.”

“She’s right over…” Sam looked to the bar, but you were nowhere to be seen.

“I fuckin’ _told_ you, man.” Dean growled, hitting Sam’s chest and rushing away to try to find you.

Sam shook his head, glared at Ruby and stomped away.

~~~~~~~~~~~~~~~~~~~~~

“Tha’s a pretty dress,” a slightly slurring female voice said, causing you to look up from the koi pond you were staring at while waiting for your Uber to show up. “Where’d you get it?” She had dark brown hair and looked more like a biker than a prostitute, wearing boots and tight jeans and a shiny black leather jacket…. And instead of a Solo cup of eggnog, she had a fifth of whiskey in her fist.

“The fat chick store,” you mumbled.

“So, what’s’er name?” she dropped to the grass next to you. “You a family er fren’?”

“Y/n. I’m… a girlfriend… for some reason.” You added the last bit as she offered you the bottle. You looked at her for a minute before taking the bottle.

“Um Meg. Um a whore. Least yer not a whore,” she slurred as you brought the bottle to your lips. You hummed in agreement and swallowed a mouthful of amber liquid, just barely stopping the grimace. “Whose girlfriend?”

“Sam Winchester’s.” You handed the bottle back.

“Tha’s good. He needs a real woman, not a stick.”

You scoffed. “What?”

“His last one is a bitch. A stuck-up sticky bitch. An’ she gives whores a bad name. How you gonna give _whores_ a bad name?”

“Ruby Two is incredibly terrible.” A gravelly male voice approached from behind you and you turned to see a man with fluffy brown hair, blue eyes and chapped lips. “She was a horrid influence on Sam.”

“Ruby Two? Why do you call her ‘Ruby Two’?”

“Because Ruby Bundy already worked for Ellen when Ruby Wilkes showed up. So Bundy became ‘Ruby One’ and Wilkes became ‘Ruby Two’.” The man said, sitting down on the other side of Meg. “I’m Castiel. You’re y/n?”

You nodded. “Which one’s Ruby Two?” you asked, but you knew. The brunette that had put her hands on Sam as soon as she walked up, the reason you left the house.

“The brown-haired one,” Castiel answered before continuing. “I believe Sam and Dean are looking for you, y/n.”

“Yeah, I just… don’t belong here, you know?”

Megan snorted, loudly. “Why, ‘cause you’re the only one here other than the Mrs. Winchester that’s never taken it up the ass for a dollar?”

“Bobby’s price point on that is quite a bit higher than a dollar.” Cas said, seriously, but you could see a twinge of a smirk in the corners of his lips.

You shook your head. “Because you all look-”

“Don’t worry about what everyone looks like,” Meg declared, words clear and firm, almost sober.

Castiel’s blue eyes pierced you as he looked over Meg to you. “This business, it forces us to see past station and looks. One cannot be shallow as an escort. You learn to find the redeeming qualities in all people. While Sam is not always the best judge in someone else’s character, Dean _is_ , and Dean finds you just as worthy as his brother does.”

You chewed on your bottom lip and looked down at the fish in the pond. “What if I don’t deserve him?”

“Then, you will have to find a reason beyond your appearance to justify feeling that way, because the elder Winchesters are the least shallow men I’ve ever met.”

“Aw, Clarence, you’re shuch a shweetie,” Meg said, leaning her head on Cas’ shoulder.

You stood, nodding at them as they got lost in each other’s embrace, and walked away toward the front yard. Your Uber driver texted to let you know he was down the street so you were going to meet him. “Y/n! There you are!” You turned, heel getting caught in the grass and causing you to tumble into Dean’s arms. “Whoa! I gotcha!” He smiled down at you, then righted you on your feet. “You okay? You smell like Meg.”

“She offered me a drink,” you said as you looked down, making sure your heel hadn’t snapped off of your shoe.

“You kinda disappeared on us,” he said, softly.

“Sam didn’t tell me that… that one of the Rubies was his ex.”

Dean nodded. “Yeah. He should have, but he likes to downplay their… _thing_ … and he really shouldn’t.”

Your phone dinged with a message from Uber. The driver was pulling in. “My, uh, my ride is here.”

“You’re leaving? Not even gonna say ‘goodbye’ to Sammy?”

You swallowed. “I’ll text him when I get home.” You shook your head. “I’m not having a very good night, Dean. First Adam, and then Ruby, and I didn’t really feel like I fit in at this party, in the first place and…”

“Let me drive you home. Send the car away, I’ll take you. I’ve heard about some bad shit happening to drunk women in Ubers.” You bit your lip, then nodded, before pulling out your phone to text the driver and let him know you weren’t going to need the taxi, after all. “Good. Come on. It’s that sexy black Impala, over there.” Dean put his arm around your shoulder and walked you to his Chevy, opening the passenger door for you and offering a hand to help you in.

You leaned your head back against the back of the bench seat and stared at the ceiling as he reversed and started driving back toward the city. Your head was swimming a little as the eggnog and whiskey caught up with you. “I’m such a fuckin’ mess.” You meant to _think_ that, but the words came out, anyway.

“How so?”

You swallowed. “I don’t know. Just feel like a mess. Sam was so excited about this fuckin’ party and here I am, running away from it so I don’t have to face the kind of women I’m never gonna be.”

“Sam doesn’t want you to be that kinda woman. I mean, a lot of Ellen’s chicks are pretty okay, but you aren’t them.”

“His ex is. His ex is so not me.”

“He didn’t tell you anything about her?”

You shook your head. “He told me about Jessica, his Stanford girlfriend, but not… not Ruby Two.”

“Ruby Two wasn't… Sam doesn’t count her as a girlfriend because he didn’t care about her. He fucked her and she damn near ruined his life, but she wasn’t his girlfriend.” There was thick sarcasm in his tone and you sighed.

“How’d she almost ruin his life?”

Dean hesitated and it made you look toward him. “It ain’t mine to tell, sweetheart, but… it’s not something he can just get over. It’s a rest-of-his-life problem and there’s no way in Hell he would want you to be anything like the woman who gave it to him.”

Your mind turned to STDs, but the intelligent part of your brain that hadn’t shut down from the alcohol yet said Bobby wouldn’t have him still working if he had herpes or HIV or something. You directed Dean to your apartment and he walked you to the door. “Thank you for taking me home, Dean. It was very nice of you to make sure I got here safely.”

“Well, I… I couldn’t let you get in a car with some dude you never met. Not with that much liquor in you, wearing that sexy dress… and the fuckin’ makeup…” His words trailed off as he dragged his eyes down your body. “And those heels are awesome… what was the question?”

You chuckled and leaned forward to wrap your arms around him. “You’re an amazing man,” you whispered as you looked up into his sparkling green eyes. You thought, for just a second, that Bobby should put the full faces on the website because the Winchesters all had spellbinding eyes, and then in the next second you were on your tiptoes pressing your mouth against his.

He went with it for a moment, pulling you closer and licking at your bottom lip, but then he removed himself entirely, hands on your shoulders and arms outstretched to keep you at a distance. “You’re gonna regret that when you’re sober, y/n. Why don’t you go in, drink some water, I’ll send Sammy your way, okay?”

You nodded and he pulled his hands back, letting you go into your apartment. Dean let out a heavy sigh and pulled his phone out as he walked back to his Chevy. Sam didn’t greet him when the call connected, jumping straight into “Where are you? Did you find her?”

“Yeah, I just dropped her off at her apartment. Meg got to her before I did, so she’s pretty smashed.” Dean licked his lips. “And remember that when I tell you this next thing, okay? She is completely drunk… and she kissed me.”

“ _What_?!”

“You know Meg drinks that 151 proof shit and y/n obviously wasn’t ready for it to be that strong and I walked her to her door and-”

“Why the fuck did you take her anywhere, Dean? She’s not-”

“Because it was me driving or some skeevy Uber driver, Sam! She was leaving, either way, wouldn’t you rather someone you trust take her home?!”

“Trust?! You kissed my girlfriend!”

“ _She_ kissed _me_ , not the other way. I sent her inside after she-”

“And I’m sure you pushed her away immediately, didn’t you? You didn’t kiss back, at all, right? You just-”

“Of _course_ I kissed her back, Sam. That’s what you do when a gorgeous woman kisses you, but it was only for, like, two seconds and then I sent her inside and _immediately_ called you. I could’ve kept it a secret, but I’m not your little college buddy, I’m not trying to take your woman, and this doesn’t have to be a big deal, ‘cause she is _drunk_ and it was just a damn kiss.”

There was silence on both sides of the phone call before Sam sighed. “Thanks for taking her home, Dean. Sorry I jumped on you like that. I know you aren’t Brady and y/n isn’t Jess… just…”

“Come see your woman, Sammy. Once she’s closer to sober, you need to tell her about Ruby.”

Sam didn’t want to have that conversation. He’d rather hand you right over to Dean than explain the bronze medallion in his wallet, but his big brother was right. He should have had that conversation with you at some point over the last month, but he was trying not to scare you off. You were already incredibly understanding of his job, finding out he used to shoot heroin was probably gonna be the thing that sent you running.

Charlie let him into the apartment two hours later and pointed him to your room. He stepped over the pile of polyester and lace just inside your door and looked over at your bed, where you were dutifully drinking a large glass of water in only your bra and panties. “I’m sorry,” you whispered as Sam approached to sit on the edge of the bed.

“For leaving the party without a word… or for kissing my brother?”

You looked down. “Both, I guess. I’m… I’m a shitty girlfriend. No wonder nobody wanted me.”

“You’re not a shitty girlfriend. You just can’t hold your liquor.” He took the glass from your hands and set it on the coaster next to your alarm clock. “And I know why you left.”

“Yeah?”

“Yeah. You saw Ruby. You’re smart and she’s obvious, so you figured out there’s a history between us.” You bit your lip in subconscious affirmation. “And you thought that that must be what I like in a woman… and you got self-conscious and then you got drunk.”

You swallowed and nodded, not looking into his face. “Y/n, I fuckin’ hate Ruby. I didn’t much like her when we were together.” You looked up as he started to unbutton his shirt. “But she found me when I was in a vulnerable headspace. She faked like she was a good person, like she gave a fuck about me, but she never did. She just wanted a six-four puppet.”

He slid the shirt off of his left arm and presented you with the inside of his elbow. “She used smack to make me that puppet.” You leaned forward, noticing for the very first time the scarred marks along the two major veins there. “I almost died because of her. I _would_ have died if Dean hadn’t forced me into rehab, personally driven me to my first three months of Narcotics Anonymous meetings.” Sam sighed. “Ruby is beautiful, yeah, but she’s _rotten_ inside. _You_ ’re gorgeous all the way through. I would never want another woman like her. I just want _you_.”

Tears welled up in your eyes as you reached forward to trace his track marks. “You never said.”

“You were already being so cool about the job, I thought learning I was in recovery might have been asking too much, too soon,” he whispered.

“Sam.” You lurched forward to crawl into his lap. You looked into his eyes and he wiped his thumb under your eyes to clear the tears. “Recovery doesn’t happen in the dark. You can’t keep such an important thing hidden just because it’s ugly. How can I support you, help you heal, if I don’t know you’ve got a disease?”

“You sound almost like you know the Program,” he whispered.

“Mom was a drunk. AA saved her. 12 steps to recovery are 12 steps, either way.” Sam nodded, remembering that he and your parents were the only ones who hadn’t had wine on Thanksgiving. Ted had even poured TJ a glass of Moscato. You ran your hands through his hair and smiled softly. “You should’ve said. If I’d know about Ruby, I wouldn’t have run from her… I would’ve put my foot up that drug pusher’s ass, and I had on those big heels so it would’ve hurt.”

Sam smiled. “You’re _so_ not a shitty girlfriend.”

You chuckled, smiling brightly. “All right. Let’s see it.” You slipped off of his lap and stood in front of him with your hand out.

“See what?”

“Your poker chip! I wanna see your recovery medal.” Sam smiled as he pulled his wallet out of his pocket and dug the bronze medallion out of one of the card slots. You ran your thumb over the ‘6 months’ in the middle, surrounded by the words ‘God’, ‘Self’, ‘Freedom’, ‘Goodwill’, ‘Society’, and ‘Service’. “Six months! That’s amazing!”

“Well, it took me a year and a half to get to six months, so…”

You smiled. “My mom got her one week chip _seventeen_ times, Sam. Progress is progress and this-” You held up the medallion. “-is amazing progress.”

He reached forward and pulled you against him. “Where the fuck have you been my whole life?”

“Right here.” You moved to straddle his lap, wrapping your arms around his neck. “Where’ve you been _my_ whole life?”

“Waiting for you,” he answered, pressing his lips to yours. You leaned your body into the kiss, into him, suddenly very aware of the fact that you were in just your underclothes. He pulled back, looking at you with lust-blown eyes. “Wish you’d left the dress on. You looked so fuckin’ good in that thing, babe. Wanted to bend you over and just take you.”

“I could put it back on,” you offered with a smirk.

“No.” Sam shook his head. “I mean, you’re already half naked. Might as well get you the rest of the way nude.”

“And you, Mr. Winchester.” You reached behind your back and unhooked your bra, slipping it down your arms and dropping it to floor next to the bed. He pulled the button-up off the rest of the way and grabbed the back of his black undershirt, throwing them on the floor, too. He wrapped his arms around you and pulled you against him, burying his face in your chest and giving biting kisses to your breasts. “Sam,” you whined as he sucked your nipple into his mouth. He bucked up against you as grinded down on his hard cock through the black slacks he wore to the party. He grabbed your hip and forced you down harder, rutting upwards as his teeth came down on your sensitive nipple, tongue swirling around it in a soothing motion immediately after. “Fuck!”

He hummed, releasing your breast with a loud, wet, pop and leaning back to put enough space between you that he could open up his pants and release his cock from his boxer-briefs. You slid off of his lap, dropping to your knees and tucking your fingers into his pockets to tug his slacks down his legs. His dick always seemed so much bigger when when you were down on your knees, with it eye level and hard as stone. You never fit it all in your mouth and you’d choked that one time you pushed your limits, but you’d gotten very good at using your hands in conjunction with your mouth to pull groans and moans out of Sam. A twist of your wrists, with a hard suck to the head, open-mouth kisses and licks with jerking motions of your hand, gentle massaging action to his balls.

You always knew you were doing a good job when his hand went from gently coaxing the motion of your head to twisted in your hair insisting upon the placement of your mouth. And when he yanked, hard, on your hair, that’s when you knew your turn was coming. That’s when you ended up on your back, Sam’s face between your legs, broad shoulders preventing your thighs from closing. Sometimes your panties would be gone, tossed behind Sam’s back like he loved to do with all of the clothing he pulled from your body, but sometimes he kept the panties on, licking at your clit through the material and leaving the fabric a wet mess of saliva and your own slick wetness. Those were the times when he’d just pull your panties to the side and fuck you beside them, with the wet cotton rubbing against his cock as it disappeared into you.

You decided, as Sam hammered into you grunting out praises of how amazing you felt wrapped around him, that you were going to need a better bed frame if Sam was going to come over ever again. Your full size bed had a pine wood frame that you had since you moved out of your parents’ house and, if the cracking and creaking sounds emanating from the wood was any indication, there wasn’t enough life left in it to handle Sam Winchester’s voracious sex.

“You gonna cum, y/n? You gonna cum all over my cock?”

“Ye-yes.”

“Gonna say ‘please’ so I’ll give that pretty clit some attention?”

“Please, Sam.”

He wedged his hand between your bodies and rubbed circles around your bundle of nerves, making you scream as your orgasm crashed over you. “That’s right, babe. Such a pretty sound. Fuck, I love it when you scream.” He kissed across your jaw as you reached behind his back and dragged your nails roughly down the ridges of muscle there. His pace stuttered, signaling that he was almost to his own end, and you clenched your pussy muscles to send him over the edge with a roar that rumbled through your body.

“Oh, god. That was… wow.”

“Better than usual.” Sam agreed, kissing your neck and shoulder. He leaned up on his elbows, looking down at you. “I think it’s because I realized I love you, y/n.” Your eyes went wide at the declaration. “I know it’s only been a month, but… I _know_. How I feel about you, y/n, it’s love. The jealousy, the fear of losing you, the way I want to destroy every person who’s ever been rude to you… how you make me feel like I’m not irredeemable, and I can be the person God made me to be… y/n, I feel cleansed when I’m with you.”

You blinked up at him, shocked. “Sam…”

“You don’t have to say it. You don’t have to say it back.”

You shook your head. “I just… I just don’t think this is the time… and… I… I don’t want to say _that_ as, just as a response to you saying it. When I say that, I want there to be no doubts.”

But that wasn’t _quite_ the truth. You knew the Program. NA kept ‘Obsession’ in the same category as ‘Addiction’, and Sam’s words didn’t sound like healthy love. They sounded like a different aspect of his disease.

Sam smiled and pulled out of you, pulling the condom off and tying a knot in it. “What are you doing New Years Eve? I got an invite to this great party at Roman Enterprises.”

“Oh, really?” You sat up as he moved to drop the condom in your trash can. “You know that’s where Charlie works. She’s the head geek in charge over there. I went to the New Years party last year and it was amazing! Free booze, which you can’t drink, a balloon drop with cool prizes, a Christmas photo booth, oooh and karaoke, which gets really funny about two hours in when people start struggling with the words to ‘Grandma Got Run Over By A Reindeer’.” You smiled as he dropped next to you on the bed and wrapped his arms around you. “It’ll be nice to have another familiar face around, since Charlie always leaves me to chase straight girls’ skirts.”

“Doesn’t she know that’s futile?”

“She loves a challenge. And a lot more chicks try it out than you would expect.”

“Has she gotten _you_ to try it?”

You chuckled. “If it were gonna happen, I’d be with Charlie, but no. Not yet, anyway.”

Sam raised his eyebrows. “I’ve got enough to worry about from you and Dean, don’t make me suspicious of your roommate, too.”

You laughed. “Oh, hush, Sam. I’m yours. You got nothing to worry about. I’m not a shitty girlfriend, remember?”

“You’re the perfect girlfriend.” He closed his eyes and tucked you tight against his body. As Sam fell asleep, warming your back, you couldn’t help but replay his words, his declaration of love. You decided, as you were finally letting your eyes close, that you would have to find out who his sponsor was and have a conversation with them. Everything would be fine, as long as you got the information you needed to help Sam. 

* * *

Stay tuned for part three!!!!!!


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